Acta Cryst. (2007). E63, o3357 [ doi:10.1107/S1600536807030772 ]
The aryl and oxazolidine rings in the title compound, C10H10N2O2, are essentially coplanar [dihedral angle = 3.8 (6)°]. The crystal structure involves intra- and intermolecular N-H
O hydrogen bonds.
N-Benzoyl-N'-(2-hydroxy-ethyl)thiourea was reacted with dicyclohexylcarbodiimide under weakly basic conditions in CH3CN to give (I) in 90% yield. Single crystals suitable for the X-ray diffraction study were obtained by slow evaporation of an acetone/water solution of (I).
All the H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.97 Å and and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(carrier atom).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
![[Figure 1]](./tk2168fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and 30% probability displacement ellipsoids. |
| C10H10N2O2 | Dx = 1.338 Mg m−3 |
| Mr = 190.20 | Melting point = 411–412 K |
| Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ab 2ac | Cell parameters from 1672 reflections |
| a = 11.4194 (18) Å | θ = 3.3–22.3° |
| b = 20.590 (3) Å | µ = 0.10 mm−1 |
| c = 8.0325 (13) Å | T = 293 K |
| V = 1888.7 (5) Å3 | Block, colorless |
| Z = 8 | 0.25 × 0.23 × 0.18 mm |
| F(000) = 800 |
| Bruker SMART APEX CCD area-detector diffractometer | 1850 independent reflections |
| Radiation source: sealed tube | 1091 reflections with I > 2σ(I) |
| graphite | Rint = 0.095 |
| φ and ω scans | θmax = 26.0°, θmin = 2.0° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −8→14 |
| Tmin = 0.973, Tmax = 0.988 | k = −25→25 |
| 9475 measured reflections | l = −9→9 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
| wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.064P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.91 | (Δ/σ)max < 0.001 |
| 1850 reflections | Δρmax = 0.15 e Å−3 |
| 128 parameters | Δρmin = −0.13 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0047 (12) |
| C10H10N2O2 | V = 1888.7 (5) Å3 |
| Mr = 190.20 | Z = 8 |
| Orthorhombic, Pccn | Mo Kα radiation |
| a = 11.4194 (18) Å | µ = 0.10 mm−1 |
| b = 20.590 (3) Å | T = 293 K |
| c = 8.0325 (13) Å | 0.25 × 0.23 × 0.18 mm |
| Bruker SMART APEX CCD area-detector diffractometer | 1850 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1091 reflections with I > 2σ(I) |
| Tmin = 0.973, Tmax = 0.988 | Rint = 0.095 |
| 9475 measured reflections | θmax = 26.0° |
| R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
| wR(F2) = 0.122 | Δρmax = 0.15 e Å−3 |
| S = 0.91 | Δρmin = −0.13 e Å−3 |
| 1850 reflections | Absolute structure: ? |
| 128 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.34177 (19) | 0.35640 (11) | 0.2998 (3) | 0.0796 (7) | |
| H1 | 0.3107 | 0.3467 | 0.1958 | 0.096* | |
| C2 | 0.33903 (19) | 0.41901 (11) | 0.3592 (3) | 0.0792 (7) | |
| H2 | 0.3060 | 0.4518 | 0.2948 | 0.095* | |
| C3 | 0.38492 (17) | 0.43353 (9) | 0.5133 (2) | 0.0652 (5) | |
| H3 | 0.3824 | 0.4760 | 0.5523 | 0.078* | |
| C4 | 0.43460 (15) | 0.38564 (8) | 0.6105 (2) | 0.0518 (5) | |
| C5 | 0.43765 (17) | 0.32282 (9) | 0.5492 (2) | 0.0606 (5) | |
| H5 | 0.4716 | 0.2900 | 0.6123 | 0.073* | |
| C6 | 0.3907 (2) | 0.30858 (10) | 0.3953 (3) | 0.0734 (6) | |
| H6 | 0.3923 | 0.2661 | 0.3561 | 0.088* | |
| C7 | 0.48292 (16) | 0.40198 (8) | 0.7777 (2) | 0.0539 (5) | |
| C8 | 0.58435 (15) | 0.35996 (8) | 1.0000 (2) | 0.0514 (5) | |
| C9 | 0.6620 (2) | 0.39852 (9) | 1.2444 (2) | 0.0701 (6) | |
| H9A | 0.6106 | 0.4059 | 1.3387 | 0.084* | |
| H9B | 0.7325 | 0.4243 | 1.2574 | 0.084* | |
| C10 | 0.69031 (19) | 0.32699 (9) | 1.2239 (2) | 0.0709 (6) | |
| H10A | 0.7742 | 0.3204 | 1.2149 | 0.085* | |
| H10B | 0.6611 | 0.3021 | 1.3177 | 0.085* | |
| N1 | 0.60390 (14) | 0.41239 (7) | 1.08905 (18) | 0.0630 (5) | |
| H11 | 0.5746 | 0.4494 | 1.0618 | 0.076* | |
| N2 | 0.53248 (13) | 0.35040 (7) | 0.85798 (18) | 0.0557 (4) | |
| O1 | 0.47644 (13) | 0.45792 (6) | 0.83169 (16) | 0.0782 (5) | |
| O2 | 0.63240 (12) | 0.30804 (6) | 1.07298 (15) | 0.0702 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0837 (16) | 0.0822 (17) | 0.0728 (14) | 0.0054 (13) | −0.0193 (12) | −0.0120 (12) |
| C2 | 0.0868 (16) | 0.0684 (15) | 0.0823 (15) | 0.0118 (12) | −0.0207 (13) | 0.0051 (12) |
| C3 | 0.0741 (13) | 0.0489 (11) | 0.0725 (12) | 0.0070 (10) | −0.0089 (11) | −0.0020 (10) |
| C4 | 0.0559 (11) | 0.0425 (10) | 0.0568 (10) | 0.0018 (8) | 0.0024 (9) | −0.0010 (8) |
| C5 | 0.0740 (13) | 0.0465 (11) | 0.0613 (11) | 0.0053 (9) | −0.0016 (10) | −0.0052 (9) |
| C6 | 0.0869 (15) | 0.0582 (13) | 0.0749 (13) | 0.0031 (11) | −0.0054 (12) | −0.0148 (10) |
| C7 | 0.0604 (12) | 0.0413 (10) | 0.0601 (11) | 0.0024 (8) | 0.0036 (9) | −0.0008 (8) |
| C8 | 0.0566 (11) | 0.0381 (10) | 0.0595 (11) | 0.0041 (8) | 0.0055 (9) | −0.0014 (8) |
| C9 | 0.0838 (15) | 0.0544 (12) | 0.0723 (13) | 0.0090 (10) | −0.0162 (11) | −0.0075 (10) |
| C10 | 0.0814 (14) | 0.0557 (12) | 0.0756 (13) | 0.0105 (10) | −0.0195 (11) | −0.0054 (10) |
| N1 | 0.0832 (12) | 0.0403 (9) | 0.0655 (9) | 0.0110 (8) | −0.0120 (9) | −0.0057 (7) |
| N2 | 0.0694 (10) | 0.0404 (9) | 0.0572 (9) | 0.0036 (7) | −0.0051 (8) | −0.0042 (7) |
| O1 | 0.1163 (12) | 0.0400 (8) | 0.0782 (9) | 0.0130 (8) | −0.0197 (8) | −0.0105 (6) |
| O2 | 0.0925 (10) | 0.0420 (7) | 0.0760 (9) | 0.0129 (6) | −0.0233 (8) | −0.0034 (6) |
| C1—C6 | 1.367 (3) | C7—N2 | 1.365 (2) |
| C1—C2 | 1.375 (3) | C8—N2 | 1.301 (2) |
| C1—H1 | 0.9300 | C8—N1 | 1.314 (2) |
| C2—C3 | 1.377 (3) | C8—O2 | 1.3368 (19) |
| C2—H2 | 0.9300 | C9—N1 | 1.442 (2) |
| C3—C4 | 1.380 (2) | C9—C10 | 1.517 (2) |
| C3—H3 | 0.9300 | C9—H9A | 0.9700 |
| C4—C5 | 1.384 (2) | C9—H9B | 0.9700 |
| C4—C7 | 1.491 (2) | C10—O2 | 1.435 (2) |
| C5—C6 | 1.379 (2) | C10—H10A | 0.9700 |
| C5—H5 | 0.9300 | C10—H10B | 0.9700 |
| C6—H6 | 0.9300 | N1—H11 | 0.8599 |
| C7—O1 | 1.2328 (19) | ||
| C6—C1—C2 | 119.4 (2) | N2—C8—N1 | 132.76 (16) |
| C6—C1—H1 | 120.3 | N2—C8—O2 | 116.77 (15) |
| C2—C1—H1 | 120.3 | N1—C8—O2 | 110.42 (16) |
| C1—C2—C3 | 120.44 (19) | N1—C9—C10 | 101.33 (15) |
| C1—C2—H2 | 119.8 | N1—C9—H9A | 111.5 |
| C3—C2—H2 | 119.8 | C10—C9—H9A | 111.5 |
| C2—C3—C4 | 120.66 (18) | N1—C9—H9B | 111.5 |
| C2—C3—H3 | 119.7 | C10—C9—H9B | 111.5 |
| C4—C3—H3 | 119.7 | H9A—C9—H9B | 109.3 |
| C3—C4—C5 | 118.47 (17) | O2—C10—C9 | 104.92 (14) |
| C3—C4—C7 | 120.05 (16) | O2—C10—H10A | 110.8 |
| C5—C4—C7 | 121.48 (16) | C9—C10—H10A | 110.8 |
| C6—C5—C4 | 120.52 (17) | O2—C10—H10B | 110.8 |
| C6—C5—H5 | 119.7 | C9—C10—H10B | 110.8 |
| C4—C5—H5 | 119.7 | H10A—C10—H10B | 108.8 |
| C1—C6—C5 | 120.6 (2) | C8—N1—C9 | 112.72 (15) |
| C1—C6—H6 | 119.7 | C8—N1—H11 | 121.5 |
| C5—C6—H6 | 119.7 | C9—N1—H11 | 125.1 |
| O1—C7—N2 | 125.85 (17) | C8—N2—C7 | 119.04 (14) |
| O1—C7—C4 | 120.36 (16) | C8—O2—C10 | 109.99 (14) |
| N2—C7—C4 | 113.79 (15) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H11···O1 | 0.86 | 2.17 | 2.696 (2) | 119 |
| N1—H11···O1i | 0.86 | 2.17 | 2.8944 (19) | 142 |
| Symmetry codes: (i) −x+1, −y+1, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H11···O1 | 0.86 | 2.17 | 2.696 (2) | 119 |
| N1—H11···O1i | 0.86 | 2.17 | 2.8944 (19) | 142 |
| Symmetry codes: (i) −x+1, −y+1, −z+2. |
The author thanks the Department of Science and Technology of Hexi University for financial support.
Allen, F. H. (2002). Acta Cryst. B58, 380–388.
Bruker (2000). SMART (Version 5.618), SAINT (Version 6.02), SADABS (Version X.XX) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.
Jiang, J. L., Duan, C. X., Li, Y. Z., Bai, J. F. & Pan, Y. (2006). Anal. Sci. 22, x119–x120.
Lorente, A., Galan, C., Fonseea, I. & Sanz-Aparicio, J. (1995). Can. J. Chem. 73, 1546–1555.(Version X.XX)
Zhang, Y. M., Xian, L., Wei, T. B. & Yu, K. B. (2004). or (2003).??? J. Chem. Res. pp. 798–799. Please check date; 2004 in Comment section in CIF.
The X-ray crystallographic structure of the title compound, (I) (Fig. 1), has not been published previously, although the deprotonated molecule has been reported in two metal complexes, namely, trans-bis(2-benzamido)oxazoline metal(II) where M = Ni (Jiang et al., 2006) and M = Cu (Zhang et al., 2004).
The bond lengths and angles have the usual values found for structurally similar molecules in the Cambridge Structural Database (CSD Version 5.24; Allen, 2002). Because of the existence of a conjugated system, the N1—C8 [1.314 (2) Å] and N2—C8 [1.301 (2) Å] bond distances are significantly shorter than the typical Csp2—N bond distance (1.426 Å; Lorente et al., 1995). The dihedral angle between the aryl rings and the oxazolidine ring is 2.856 (3)° and the C4—C7—N2—C8 torsion angle is 175.45 (2)°.
An intramolecular N1—H11···O1 hydrogen bond is found and centrosymmetrically related molecules are connected via N—H···O hydrogen bonds involving the same atoms (Table 1).